Patreon LogoYour support makes Blue Moon possible (Patreon)

A much needed change (Floss88 x lasciel)

He almost sounded defeated. Had the infamous Samuel Adam Cauldwell, of Drax, Bundy and Cauldwell, gone down so easily? It had to be the alcohol coursing through his bloodstream, Catherine was sure. That, or he'd been spending cycles on her beyond just his incessant propositions at the weekend-edge of each of their meetings. Clearly he hadn't been thinking about this, but if she'd crossed his thoughts at all in more than just a professional sense, she could see his relief at finally getting what he thought he wanted leading to some... unexpected behavior.

Or I've found out Sam's deepest, darkest secret.

God, but that little gasp he gave made her loins burn. She didn't feel the same building need to cum that he did, but that didn't stop her clit from throbbing between her legs, or slickness from making her lower lips rub against one-another as she shifted her position behind his chair. While her plan had been simply to ruin him in whatever ways he allowed her to, she finally began to ponder whether she should make him earn his climax as a more proper pet would.

"Are you begging, Sam?" She asked softly, genuine wonder giving her husky whisper a strange inflection. In deference to his request she held still, not wanting to push him accidentally over the edge just yet. "And to not let you cum, at that." Catherine added in a sigh, and even if he couldn't see her face from the angle she was at the smile in her voice was obvious.

"Well..." her green eyes looked up from beneath a curtain of painted-dark lashes to the towels and duffel sitting untouched on the far couch. "I suppose, if I were you, I'd also be desperately curious to find out what's in that bag. That's what this is about, isn't it?" She rubbed her palm against him once, then stilled again. "And you know that once you finish, the spell will be broken, the carriage turns into a pumpkin, and this little fantasy of your ends." Her hand made another slow circle in punctuation. "A bag introduced in the first chapter must be opened by the third." Her inebriated mind couldn't quite produce the exact quote by Chekhov, but another roll of her wrist ensured Sam wouldn't be complaining.

"So tell me, Mister Cauldwell..." Catherine switched her grip again, holding his shaft with four fingers and her palm and rubbing only her thumb now over the head, across the slit where precum left her thumbtip slick. "Do you think you've earned the right to find out what's in that bag?"
 
"Yes," He panted slightly as she slowed, thank god, if she needed him to say he was begging to slow down he could do that. "Yes Miss Jones, please." She was enjoying this, enjoying his suffering for want of a better word. He should be mad about that, at least a little, instead his brain just clicked like he was solving a puzzle so that's how I turn her on'. He was starting the view this game entirely differently, less as something to get through than a means to win by making Miss Jones cum. Just as he felt he was getting somewhere though, starting to get his head around the game she began again.

The bag, he had forgotten the bag.

Sam was so distracted by the teasing and the feel of her hard body against his that he had forgotten her ominous entrance. She was right though he had to know, his eyes darted to the bag as if it was going to leap up and do something of its own accord. Since her entrance though it had gradually become clear to him that whatever Catherine was into it was far beyond merely being the reverse of those girls who liked to fuck with their hands tied over their heads. He should perhaps have expected that everything he knew about the woman professionally told him she wasn't the type to do anything by half measures. He had to admit it, even if only to himself, that the contents of that bag were probably something well beyond the pale of his sexual experience.

"Earned the..." Sam said out loud without thinking genuine confusion in his voice. This felt like something he was supposed to know to answer too. A moment later he got it and spoke more strongly, though still breathing heavily as she played with his cock like it was her personal toy. "I've done as I've been told Miss Jones but... I don't know if that's enough to earn anything?" He paused very slightly between each word, tentatively feeling the idea out as he spoke. He tried but failed, not to say it as a question he didn't want to take her out of the moment any more than he wanted to cum himself.
 
In contrast, she hadn't thought about him professionally in several minutes. But the way Sam worded his response, once he'd collected his thoughts, reminded her a bit of the cunning mind currently smothered beneath a blanket of thick arousal and frustration. And if he'd avoided that little inflection at the end, she might have even taken him seriously.

"You're finally catching on." Catherine said, patting his cockhead twice with her fingertips as if it had just performed a trick. Then she withdrew. "Keep stroking..."

The dulled click of her heels on the rug took her around the back of his chair, but rather than coming to the front she crossed past the coffee table to the couch. Pushing the bag to the side, for now, she took one of the towels and laid it over one of the cushions, which she then promptly sat on with her ankles crossed tight. "What you've earned so far is me not forcing you to paint your own chest and then sending you home. And what is earned can be lost, mind you."

Catherine reclined further into the couch, stretching her arms over the back in both directions and uncrossing her legs in an obvious power-pose. The few tasteful objets d'art on the coffee table failed to obscure Sam's view, and he learned two things about his counterpart in that moment.

The first was that she'd changed out of more than just her button-down between their time in the conference room and their chance meeting at Narcissus.

And the second was that the carpet did, in fact, match the drapes.

Still hiked partially up her thighs from when she'd knelt one leg between his knees, her pencil skirt provided no modesty in her current position. He could see that the hose she wore with it's alluring back seams was in fact a pair of thigh-highs, held up along muscular legs with the aid of a black lacy garter belt. Otherwise, there was nothing obstructing his view of her pale inner-thighs and the pinkness of her small folds save for a neatly-trimmed trimmed patch of auburn curls at her mons but not extending any further.

"If you want to earn more than that, come here and prove it." She ordered when she thought he'd looked his fill. Crooking one finger, when he'd stood she changed to point down at the space between her legs on the rug. Even given Sam's rather patriarchal sensibilities Catherine assumed he knew what was coming next. Spreading her legs a little further, shifting her hips forward, and hiking her skirt up to her hips she hoped would clarify any lingering doubt. The two fingers she pressed against her outer lips, spreading herself and exposing her swollen nub, were the double-underscore to her obvious message.

Except for one little catch. It wasn't like he needed both hands in addition to his mouth to please her, anyway.

"Though, Sam..." She drawled, pressing the ball of one stocking-clad foot to his chest before he could lean forwards. "Don't stop stroking." She let her leg drop and waited for him to comply.
 
So he was doing, ok, if not well. She wasn't going to send him home just yet at least, a possibility which had been haunting the back of his mind. Normally by the time you've got back to someone's apartment, it is reasonable to assume you will at least be sleeping there but the evening had diverged from normal some ways back. So Sam merely nodded and reluctantly pumped his cock, slow but steady and gripping hard as if that was a means of control.

His focus was on her though, she stalked around to sit across from him. Even ostensibly fully dressed she was so damn hot, his mind's eye filling in details only hinted at by curves of fabric. He wanted her and nothing about his gaze concealed that. As she sat across from him the dynamic could not have been more apparent, she sat like an empress in total command of all she surveyed arms spread wide, while he was naked and jerking off to the mere sight of her. If he felt shame or embarrassment though they were drowned under waves of arousal, he wanted her, wanted to fuck her so badly any terms and conditions attached seemed worth it.

Then she opened her legs and Sam bit his lip and stared with absolute focus. God, she had such a perfect fucking pussy, framed by pale muscular legs in thigh high stockings he currently wanted it in any way possible more than anything in the world. Finally, he had wanted to see her pussy since the first day they met months ago and somehow it didn't sate him at all now he just wanted more. Now she was giving him a chance to earn it.

"Yes Miss Jones, thank you Miss Jones" the words came out quicker than intended, he was so glad to be out of the damn chair and to get go of his throbbing cock if only for a moment.

He nearly stood up but instantly realized that would be wrong. He might not really understand what was happening but he could at least pick out the artistic themes. Sam slid out of the chair and onto his knees, careful to never have his body higher than Catherine's eye line. He crawled across the floor flexing and tensing his body with exaggerated care, trying to show off the physique he was so proud of. She wanted him naked for a reason after all. As he finally got there, having the push the table back slightly to make space for him to kneel at the feet of his rival, she spread her lips apart and Sam groaned just slightly. Something about the teasing, every sexual thing she did now hit him as impossibly sexy, almost too much to deal with.

He started forward, his mouth opening and she spoke again. Damn,

"Yes, Miss Jones" Was all he said, not even trying to keep reluctance from his voice. Sam placed one hand flat on the ground, the other wrapped around his cock, and spread his knees wide to get himself low enough. Finally, he felt like he had permission and it was like a dog being let off the leash at the park, lapping, sucking, and licking with ferocious energy. He would be lying if he said the desire was entirely altruistic he wanted her to feel what he felt some of this burning insatiable arousal she seemed not to be suffering under.

He wanted her to cum, but more than that he wanted to make her cum. At least that's what he was telling himself as he licked at her pussy like it was the only source of water in 1000 miles, his knees pressed into the hard marble floor and his hand pumping his hard cock, he told himself he had some measure of control or influence.
 
She'd seen men look at her from similar positions with equal hunger, but something about Sam hit her differently. It was the contrast, she realized, between the man he was in the conference room, and the role he was playing now. Professionally, she respected him. He was good at his job, if infuriating to work with/against at times, and every ounce the type-A personality who acted like he was owed the world while still being able to actually cash the checks he wrote. Personally, she wanted to grind him under her heel. And he was doing a good job of granting her that wish, which was something she never would've expected based on everything else she knew about him.

And damn if the man didn't make it look good to obey. Whatever fitness routine he kept to clearly had an emphasis on mobility as well as strength and physique, as he moved with a panther's grace across the living room towards her. He was showing off, clearly, but it was a show Catherine approved of. And she rewarded him with a look of hunger to equal his own, no longer seeing any reason to hide the effect his submission clearly had on her.

Fuck, she'd been looking forward to this. It was her turn to bite her lip in anticipation and desire, staring down along her own torso to watch as he adjusted his position to the point where he could still touch himself and service her. Those storm-grey eyes still held the barest hint of defiance... she'd have that out of him by the evening's end, though. But she liked that he still had some fight in him. He would've disappointed her deeply, otherwise.

"Ah, fuck..." As he went to work the word escaped her thoughts and came out in a low sigh as her other hand found the back of his scalp and her fingers wove once more through his thick, black hair. For many minutes after that the only sounds in the room were from his stroking and licking, and her increasingly heavy breathing.

"For a man who, mmm, sounds less-than-interesting in pleasing his nightly conquests, you're not bad at this." Catherine finally declared in a surprised, husky voice. He'd earned the praise, begrudging as it was. Whatever advantage he'd started off with by her being already thoroughly turned-on had been mediated by the effect alcohol had on her sensitivity. Already a tough customer by her own quirks of genetics, the heavy drinking she'd engaged in had left her worried that Sam's presumably mediocre skills would leave her frustrated. But he was making good progress, judging by the wetness he'd coaxed from her core and the way her thighs occasionally trembled on either side of his head.

Actually making her cum, though, was another privilege he hadn't yet earned. And if she left him stroking for much longer she was sure he'd have an accident the moment she so much as tried to tease him. So with some reluctance she moved her hand from the crown of his head to his forehead, pushing him back and away to look up at her instead.

"If you are good, I'll let you finish that job later." She watched his face for any hint of his feelings on the subject. Catherine still wasn't sure if his enthusiasm was for wanting to please her (so he'd get what he assumed was coming), or for wanting to make her finish out of some sort of competitive urge. Maybe he thought if she climaxed she'd take pity on him. From how she knew him, she would've bet good money on the competitive aspect, but nothing about the way he'd acted since they'd crossed her doorway had been as she'd expected.

"Hands down by your sides."

She swung one shapely leg over him, and with both on the same side of his knees she stood. Looking down at where he knelt she quietly chuckled to herself, then took a few steps away and put her hands on her hips as she surveyed the scene. First Sam, then the bag, the latter of which she strode over to and unzipped. From his vantage on the floor he couldn't get a good look inside, but he could see what she withdrew: nitrile gloves and a bottle of water-based lubricant.

"Once more, mister Cauldwell, I will remind you that if you want things to stop, you only need say the word." Both items were placed on the coffee table as she spoke, and then the bag closed once more. Then she looked down at him, and gestured at the towel-clad spot on the couch. "Up. On your knees, hands on the back. If you're confused, just think of how you wanted me positioned in your little fantasy." She turned back to her items, pulling a glove over her right hand with a loud snap for effect.
 
As she pushed him back Sam couldn't hide the confusion on his face. Did she not want to finish? A slightly teenage thought rolled through his mind, isn't never worrying about finishing the point of multiple orgasams? But is was quickly suppressed by her words. Eating her out was a privilege by the sounds of it, at any other time he'd have been irritated or cracked a joke about her hubris. Yet the fact he wished she had let him finish her, make her cum was undeniable he did want to dive back in to keep going, he had to fight to tear his eyes off her gorgeous, pink, pussy and look up at her.

"Yes Miss Jones" the words came unbidden, he was getting into it by rote now. Playing a role, even if it was one he didn't fully understand. Having something to say, instructions to follow, made dealing with the increasing pressure of his own arousal. He nearly sighed with relief when she told him to place his hands at his sides.

Sam felt his mouth go dry as Catherine opened the bag and withdrew the gloves and somehow more ominously the lube. He didn't know what to do, something about this felt entirely too real... and yet. He wanted to know more, he could stop at any time sure but he got the distinct impression that stopping meant stopping. Not stopping the game and having conventional sex but stopping alltogether and Sam going home to jerk off never able to look Miss Jones in the eye again. The snap of the glove did it, his cock throbbed, he couldn't just stop but he needed... something.

"What-" he struggled through his dry mouth and sore jaw. He coughed slightly and tried again. "What is going to happen Miss Jones?" He hadn't moved from his knees which he knew was a risk but he hoped he had phrased it right.
 
Catherine couldn't tell if he looked disappointed or frustrated. Maybe both. She didn't much care which, as both suited her purpose: establishing control. She was the sole arbiter of what he got to do, to touch, when and where he got to cum, and what pleasure of hers he was allowed to experience. And despite her concerns he seemed to have picked up on the message with startling ease. Though he hadn't needed to reply, that additional Yes, Miss Jones as he dropped his hands to his sides sent a new pulse of warmth to her already heated loins, and earned him half a smirk.

That smirk faded when she saw he was still on the floor. Briefly she considered pressing the point, but even inebriated and frustrated as she was with his prior behavior she knew it would be unfair to him. He could say stop and leave at any point he wanted to, but telling him to simply do as he was told felt too close to a violation of consent for her tastes. So she squatted down, resting her elbows on her knees, to face him at his level.

"I've told you before. Whatever I want." She gave him a cheeky grin, but then continued. Leaving any confusion about what was going to happen next was a good way to get kicked in the stomach or butted in the face. As much as she disliked her own choice of language (too vulgar by half) she knew she had to be explicit. "And what I want right now is to use my fingers in your ass to make you cum harder than you ever have in your life, Mister Cauldwell." It seemed a good bet to her that he'd never had anyone else touch him back there for anything but a medical exam.

Reaching out with her gloved hand she cupped his chin and turned it up slightly. "Of course, you're free to say no, and you can leave whenever you want. I'll even let you jack off in the guest bathroom before you leave. But then, of course, you'll never find out what else is in that bag, and you certainly won't be able to feel like you got any satisfaction out of your months of dogged persistence."
 
Sam couldn't help himself he leant forward just slightly when she squatted down, even now worried about what was going to happen he wanted to be closer to her. He was a little irritated with himself, he felt out of it somehow more than the drinks should have accomplished, almost like he was playing a part on a stage. The rote replies, the constant thumping pulse of his own arousal and frankly Catherine's command of the situation was pushing him into this role where he almost didn't feel like himself. It wasn't like losing control it was more like... permission. He couldn't think about it too deeply right now, he wasn't capable about thinking of anything too deeply right now, but this sensation was totally new and alien to him and he didn't want it to end.

The way she said it. Whatever I want. Made his cock thrum like a high voltage electrical wire. This was it, this is why he had wanted to fuck her so badly, apart from her looks obviously, the sheer raging power the woman seemed to have. He had wanted to defeat it, tame it, prove he was better and move on. Right now though, in his current state, he just wanted to be near it. As she explained he had to look down, not blushing but almost embarrassed by the prospect. So he looked at the floor between her legs rather than meet her gaze. Harder than he ever had, from everything he had experienced so far tonight Catherine clearly knew what she was doing here. But he had never... He had never even thought about his own ass like that. Hell he knew about the prostate but it was mostly a thing for juvenile comedy movies to laugh at and old men to worry about.

He wrestled with it until she took his chin in the strange plastic feeling hand of the nitrile glove and brought his gaze up to meet her's. That sealed it, he didn't want to leave, he couldn't let this end with a sad wank in a bathroom. An offer he knew he would have to accept if he was going to walk around in public. In any case Catherine was right he had wanted this, well not this but her, for what in this moment felt like an age. He had to have whatever he could get, even if it was only whatever she wanted.

"I don't want to stop Miss Jones"

Silently he pulled away, mounted the couch like an animal and assumed the position he had wanted her in for so long.
 
Even with his assent she held his chin for a moment longer. Long enough to purr two more words, and then she let him pull away.

"Good boy."

Straightening and taking a step back she gave him space to get up on the couch. He did as such, and she grinned broadly as she watched his hard cock and heavy balls swing down as he raised his ass into the air. Even then there was something assertive about his position, demanding her gaze, and the appreciation of his muscled and carefully-maintained body. The pose highlighted his gluteals and hamstrings, and the muscles that ran along either side of his spine at his lower back just above his sacrum.

"I think you were right, earlier." Catherine admitted as she stepped behind him, and gripped one muscled cheek in her left hand and squeezed. "In some ways you are my type. I'm a sucker for a good ass." Her hand withdrew, then returned in a sharp smack that nevertheless lacked much of the power she could've given it. She wasn't trying to hurt or punish him.

She didn't pull away immediately, sliding her fingers towards the inside of his thigh and tracing forward along that crease to where his shaft met his lower pelvis and taking hold of his cock, which was still startlingly erect. "So hard and ready... you're going to cum like a fucking fire-hose if I let you, won't you?" She rubbed her thumb again over his head then let him go.

Behind him, Sam could hear the quiet click of the lubricant's cap opening. There was a wet sound as something was squeezed into her palm, then rubbed between and over her fingers until it had been thoroughly distributed and warmed. Nobody liked cold, sticky fingers, after all.

"Now, I need you to relax for me, Sam." Catherine's voice had a touch of softness to it, gentle encouragement rather than the sharp orders she'd been delivering before. Behind him he could feel her spread his cheeks and expose his hole. Her gloved thumb, slick with lube, rubbed a slow circle around his entrance. "Relax..."

Her thumb was replaced by her index finger, also thoroughly slicked, which pressed slowly but insistently into him. Her other bare hand reached around one muscular thigh to grab his manhood once more, pumping slowly as she penetrated him. She paused at least once to reach for the lube bottle and add a little more, and then at last she was stroking him with her finger buried past the second knuckle.

"Pay attention and tell me how that feels." Catherine paused in her stroking, though her thumb had returned to idling over his head, as she crooked her index finger. He could feel her search for something, and then press gently into a very specific firm spot against the anterior wall of his ass.
 
As the gloved hand petted his ass Sam found his back arching, trying to push his ass up to meet her hand. Trying in some perverse way to show off, he didn't think about it, he didn't think about anything really. Just dwelled on the vague sense of dread at where he found himself. He had decided to stay to, let her... well let her do whatever she wanted. But that didn't make him feel less vulnerable in this position or make the sound of her moving around behind him less ominous. The sharp slap, hardly a slap at all really but the shock made him clench his butt in response. It was like his while body was responding every time she touched him.

"Thank you Miss Jones." Sam didn't need telling his ass was outstanding. He worked hard to stay in excellent shape, a firm beleiver that it was a fundamental aspect of self respect. Still he couldn't keep the little trill of pleasure and pride out of his response. He wouldn't put it in these terms but Sam certainly enjoyed being objectified.

The wait was killing him, he know it had been almost no time at all since she told him he was a good boy and he mounted the couch. But the mix of arousal and well... Fear? Concern? Anticipation? Whatever it was was making the seconds tick by like hours. Finally she touched his cock again, he felt like he had never been this hard. He simply wasn't used to denial, it was totally new.

"Yes Miss Jones. Like a fucking fire-hose Miss Jones" he couldn't keep the slight beginnings chuckle out of his voice as he said the words fire-hose. It did as much as her next words to make him, for want of a better word, unclench. Her small, rubber wrapped hands pulling his cheeks apart still made him flinch for a second though. It was such an alien feeling, one topped almost immediately by Catherine's gentle massaging of his asshole. For a moment again he tensed up but something about the feeling and her voice calmed him back down. It was such a change, yet another side of Catherine he hadn't seen before. This thought was completely over ridden by the finger.

She worked Sam's thick cock slowly not letting him calm down as the finger penetrated him. Almost instantly he started breathing more heavily, opening his mouth to almost pant. The feeling wasn't bad, it felt good even but there was something else. Being penetrated even with just a finger was just slightly unsettling like standing on uneven, unstable ground or the edge of a tall building.

It was good, it was new certainly but he had no idea what he was supposed to say as she crooked her finger-

"JESUS FUCK" the words burst out of his panting mouth as his hands gripped the top of the sofa, his toes scrunched up and his ass clenched and unclenched around her finger. When she found his prostate he suddenly felt with incredible sensitivity parts of himself he hadn't even known he could feel. The good feeling had multiplied a hundred fold but the vague unsettling feeling rose exponentially manifesting in a knotting feeling in the pit of his stomach.

"Oh God, what the-" Sam managed before remembering himself slightly. "It feels... it feels good Miss Jones. Please."

The last word came out as a gasp. Please what Sam couldn't have told you, please stop so he wouldn't cum like this? Please don't stop because he'd never felt like this? Both? He didn't know.
 
That was more reaction than Catherine had been expected by a factor of ten, and she straightened her finger immediately as her whole body went rigid and still in fear that she'd hurt him or he'd hurt himself trying to pull away. While there were plenty of ways she'd love to have hurt Sam Cauldwell, this wasn't one of them.

But he didn't try to escape (for lack of a better word). His own thoughts seemed as surprised as hers as he spoke, paused, then remembered his surroundings. The second attempt was better, though Catherine wouldn't punish him for the first. The walls were soundproof (not that she knew if the adjacent units were even occupied, or more corp props like hers), and the rawness in his voice was something to be cherished. She'd just shown him something entirely new, and nobody else could take that first away from her.

"How good, mister Cauldwell?" She asked as her hand began to stroke again. She gave his ass another few heartbeats before she moved her fingers again, as well, stroking that magic spot inside of him very gently. Whether he was merely surprised, or particularly sensitive, was yet to be seen. Regardless, she didn't want to risk setting him off too early. "Because this is only the tip of the iceberg. With how you've been responding so far..." Catherine paused to chuckle knowingly.

When she'd turned him down, over and over again, she'd never really put any thought into what would happen if she said yes. He simply wasn't someone she'd been interested in having sex with, primarily because she'd assumed their definitions of sex were too disparate to be be worth dwelling on. But now that she'd had a taste she wanted to go all-the-way. She had to fuck him, needed to have him panting and moaning beneath her and her strap. The only question was how... her own personal rules gave her a short leash there. Coercing or pressuring him would violate her ethics.

But making him enough of a horny mess that he wouldn't say no? Well, that was another matter entirely.

"I'm confident there's more in that bag which you'd enjoy even more. Though I suppose that's moot if you're as likely as it feels like that you're just going to finish in my hand." She crooked her finger a little harder against his prostate for emphasis.
 
"Very, very good Miss Jones. Sorry I- I've never- no one has-" Sam tried a few times but he didn't know what to say, he had simply never been aware of his prostate till that moment not in the physical sense. Apparently, that was a mistake on his part, Sam's attempts to form that second sentence were consumed by a low moan he was shocked to hear himself make. Sam never made sounds like that but as Catherine's finger moved across his prostate as she worked his cock he couldn't keep the noise from rising in his chest. It still felt so unsettling and yet the jolts of sensation made him want to push back to lean into it.

If you had told Sam when he first met Catherine that he would end up here, bent over and making noises like that he would never have believed you in a million years. Hell, he probably wouldn't have believed you a few hours ago. Part of him was intensely embarrassed by the noise he made and the position he was in, he was after all a powerful dominant man but it couldn't compete with the overriding need to have this not end. He felt like when he did come he was going to come harder than he ever had in his life and made Sam want to put it off for as long as possible.

"Please don't make me finish in your hand, Miss Jones," He was under no illusions now that he was the one to control when he came, that he could make a decision on that. It was so hard to think clearly, to form his words into coherent and impactful statements. Sam had spun entirely new arguments out of the air midway through multi-million dollar negotiations numerous times without raising a sweat, but then he supposed no one had their fingers up his ass on those occasions.

Now the promise of better, of more was driving him mad. If he was being totally honest the main source of his stimulation was the sheer newness, the peculiarity, that this was not like anything else he had ever done before. What else might be in that bag, what else Catherine might have planned he had to know, he certainly wanted to see more before he came.

"What-ah- what else is in the bag Miss Jones?" Sam tried and failed to keep the slightly pleading tone out of his voice. Not that it would have mattered if he had managed it, as he finished the sentence her finger went over a ridge on the walnut of his prostate and he groaned which would to say the least have undercut any attempts at seriousness. There was just something so incapacitating about this it was like someone had a knife to his throat or he was stood on the edge of a tall building.
 
This was what she had meant by singing. And he made up for his earlier sass in spades.

"Now those are the sounds I've been waiting for." Catherine remarked with a low chuckle as he punctuated himself once more with an unintentional sound of pleasure. All of his careful poise and grace and alpha-male bullshit was... well, not gone, but suppressed. The position she'd chosen was deliberate, and she knew that he knew how exposed he looked. It was a sure bet he'd fucked women in the same pose before.

Was he thinking about that, right now, she wondered? Did he still harbor any hopeless fantasies of bending her over the back of the couch before the evening (well, morning really) ended? Part of her hoped he did, because she respected his stubbornness and perseverance and would've been disappointed to find out it was a facade. But part of her... part of her wanted to break him.

"I'm not going to make you finish anywhere, Sam. Where and when you cum is up to you and how much control you can exert over yourself. You do strike me as a very controlled man. I can't imagine my dainty little fingers could do much of anything in the face of that iron will." As she teased him she added a second finger, slower than the first and giving him plenty of time to adjust. Her slow pumping of his cock paused so she could add even more lubricant, then resumed at a sluggish pace. Despite her monologue she knew she could make him cum no matter how much control he had over himself, and she still wasn't ready to set him off yet.

"As for what's in the bag... well, those are the tools I can use to make you cum. Lots of lovely toys, though you haven't yet earned the privilege to enjoy most of them." She'd packed the bag with Dan in-mind, and Dan had something Sam was sorely lacking. Experience. Dan was an experienced bottom, and a pain-slut at times, and the variety of implements she'd packed were centered around those interests. She had no idea if Sam took pleasure in being paddled or whipped or dripped with hot wax, or how he'd take to being restrained and denied of his senses. Hell, she wasn't sure if he could even take the smallest dildo she'd actually brought.

Well, there was really only one way to find out, and getting there first required getting three fingers in him. The second fit tight, and she could curve both to press into his prostate more effectively than one alone, though she could feel her wrist beginning to tire regardless. She paused to add more lube, pulled back, then added a third and began to slowly press into his gradually-loosening sphincter. She'd stopped stroking him, to let him better focus on relaxing his muscles.

"Is that too much?" Catherine asked as she pumped her digits in and out, gaining a little more depth each time. "If it's too much tell me and I'll stop." No cruel mockery undercut her words this time. It wasn't a challenge, but a genuine question of concern as to whether she should keep going.
 
Hadn't earned the privilege to enjoy, Sam found his currently limited cognitive bandwidth consumed with the statement. There was still so much of what was going on that he didn't understand he felt like the only actor on a stage without a script. Was he supposed to want what was in the bag? or worry about what was in the bag? Sam was beginning to suspect the answer was probably both. That in itself was confusing, or at least it was while 90% of his brain was focused on the second finger entering his ass.

Sam didn't even notice when Catherine stopped stroking his cock, he was so focused on the three gloved fingers massaging his prostate he could barely think about anything else. It was so strange, like being hyper-aware and totally helpless all at the same time. He couldn't stop himself moaning and groaning as her fingers made their way across the ridges of his prostate. The noises sounded like they were coming from someone else, he just didn't recognize them. Sam had groaned occasionally while receiving a blowjob but that was deeper, controlled, sonorous. The noises he made now seem almost pleading, nervous, uncertain. Frankly, he sounded desperate.

"N-no Miss Jones." He began not sure what he was going to say but he couldn't let her stop. He didn't want it to be over any more than he wanted it to finish. "No please don't stop, please I want more. Please, Miss Jones." Sam didn't know what he meant by that the word had come out of nowhere but as soon as he said them he knew it was true.
 
He had the right of it. The answer was both, and Catherine was doing her best to ensure he was filled with a mix of worry and desire when it came to the unassuming black duffel's contents. It was something she'd missed with Dan, as he knew her tricks and he knew, generally, her tendencies. Sam was virgin territory, and she could still surprise him. He truly didn't know what was in her bag, had no idea, and teasing him with the contents was too delicious a feeling to pass up.

Of course, fucking him with the contents would be even better. That would be coming soon, she hoped. Especially with how his ass relaxed and clenched about her three fingers, leaving her hesitantly confident he could take the smallest toy she'd packed. It would be a tight fit, but given how much he seemed to melt from how she fucked him with her fingers left her optimistic at how he'd take eight (or likely fewer) inches of velvety silicone.

"You're begging again," Catherine purred, pressing her fingers a little more firmly into him. "I like that, do it some more."

Worried still about his proximity to the edge she used her second hand to stroke his back rather than his cock, petting him like a beloved dog as she pumped his hole with three fingers. He was tense, and for good reasons, but she needed him to melt a little more before she'd move on to the next stage. Those sounds he made were wonderful, though, and Catherine would admit she was also taking her time enjoying them. They were pleading and desperate and made her cunt throb with more heat than even his tongue had.

"I'll give you more, though. You've been good enough to earn that." She finally stated, pulling her fingers free and flexing them to work some of the stiffness out of her wrist before inverting the glove off of her hand entirely.

Walking back over to the bag she unzipped it once more with her off-hand, a small hole that didn't let Sam see inside as she groped blindly for what she wanted by-touch. And she found it, pulling free a dark purple phallus only vaguely suggestive of a true cock, eight inches from the flared base to the bulbous "head" but lacking balls or anything more lifelike than it's most basic shape. It was the smallest toy she'd packed and still competitive with his endowment. Well, if he balked she could always cheekily ask him how many women he'd fucked in the ass, and whether he thought himself less sturdy than they.

Transferring the dildo to her right hand she continued to search with her left, until she came up with a harness made of leather and brass and ballistic nylon. Then the bag was zippered closed, the dildo fitted into the harness, and the whole assembly set on the coffee table with the rest of the tchotchkes and out of his view as her hands went to the size-zipper of her skirt. Fucking him with the garment hiked up around her hips would just ruin the wool, and be uncomfortable to boot. If he turned his head he could see her finally strip down, high-stepping out of her skirt once she'd gotten it down to her ankles, setting it aside, then reaching behind herself to undo the closure of the tight leather bralette she'd been wearing under her since-discarded jacket.

That left Catherine wearing only a garter belt, thigh-high stockings, and the elegant black pumps he'd heard her clicking around the apartment in. The rest was more of the pale, smooth skin he'd likely imagined her with when he'd undressed her in his mind, though he could see a few imperfections like the faint appendectomy scar above her right hip, a beauty mark to the left of her spine above her sacrum, or the small dot of a scar just above her naval from when she'd had it pierced and then healed-over as an undergraduate. Her breasts were well-apportioned C's, teardrop-shaped with small pink nipples hardened from arousal. Without her skirt he could see the faint impression of abdominal muscles continuing down to her pelvis, strength telegraphed in the way torso and hip and thigh all met.

Those muscled hips were soon snugged with leather-and-nylon as she pulled on the harness she'd taken out and set up moments ago, trapping the straps of her garter beneath as she cinched down the loops. The silhouette she cut, hips tilted slightly forward with dark purple dildo jutting out, was arrogant and aggressive. Reaching down Catherine stroked the fake phallus she wielded and looked at Sam with a brow raised in challenge.

"Are you ready for me to fuck you, Sam?" She asked, rubbing her thumb over the "head" of the dildo as if she needed the stimulation to keep her toy erect. Then she came around to the back of him and he could hear her uncap the lubricant bottle and begin to slick up the hefty toy. "If you are, drop your hips and raise your head. I can't reach your gorgeous ass all the way up there." The height of his hips had been excellent for manipulating him with her fingers, but less than ideal for fucking him with her hips.
 
Sam felt so strange as she pulled her hand out of his ass, he caught himself pushing his ass back into nothing but empty air as she walked away her pumps clicking. That was embarrassing, he considered for a moment, he wasn't entirely comfortable with how he sounded, how he was acting but he also knew he wasn't even close to stopping. He might not be comfortable with it but he wanted this, whatever this was, badly.

Then he heard what he knew was coming and the bag unzipped. He tried to stay looking ahead focused on the window, her reflection was blurred against the black glass, he saw she was pulling something out and heard it clink. Sam was torn, he both desperately wanted to know what it was and was worried about what he might see if he turned. When the reflection made it clear that Catherine was finally undressing though his resolve crumbled.

As he turned back Sam saw very nearly exactly what he had fantasized about for months. Catherine wearing stockings, heels, and a garter belt. Her body was perfect, pale and toned she looked strong and powerful but also perfectly feminine. Sam had spent so many meetings wondering precisely what her tits looked like and the reality was spectacular his cock pulsed as he pictured himself wrapping his lips around her pink nipples.

All was not exactly as he imagined it though, swinging from her hips was a thick purple cock. Sam gulped involuntarily as it swung pendulously with every step Catherine took towards him. It was so big, so thick, on Catherine's smaller frame it looked colossal, intimidating. Her eyebrow arched as she saw his face and in spite of himself Sam felt cowed out of saying anything, she looked so powerful, so confident while he was holding out his ass consciously feeling the absence of her fingers.

He still didn't say anything when she asked him a question he just let out the slightest whimper as he watched her hand pump up and down the dildo like it was a real cock as Catherine lubed up her strapon. Sam didn't even think, didn't rationalize it, he just turned back towards the window, dropped his ass, and arched his back up as instructed. He felt a little burst of pride as she complimented his ass, which dissolved as he said some word he could not have imagined himself saying before tonight.

"Please Miss Jones. Please Fuck me."
 
He did it. The man did it, Samuel fucking Cauldwell gave his assent with a drop of his hips and-- and he asked her to fuck him.

With her unlubed hand she reached up and pinched one of her own nipples, curious if she was in some sort of dream or fantasy. But the sudden sting of pain was very, very real, if still blunted by her earlier drinking. Well then. Maybe she should have given him what he apparently wanted the first time he asked. Except Catherine wasn't sure things would've gone the way they were going now if she'd given in when he'd wanted her to. How much of his pliability could be ascribed to her repeated rejections? If they'd gone back to his place, as surely his plan was, she certainly wouldn't have had her tools at the very least.

"Of course, Sam. How could I turn down such a polite request?" Catherine replied with a warm chuckle, spreading his cheeks with her off-hand and lining herself up with the other, holding the base of the shaft so the toy didn't try to pivot downwards. It occurred to her that her toy was bigger than his impressive natural equipment, and she wondered if he'd realized that. Did that make it more embarrassing for him? It certainly made it hotter for her.

The lubed, bulbous head of the purple dildo kissed his entrance but she didn't push any further.

"Now Sam, I want you to listen carefully." Her hips rocked slightly, giving him just a bit of pressure without the satisfaction of penetration. "If anything hurts, I want you to tell me right away. We'll go back to something less intense."

She didn't want him holding back from telling her if there was a problem because he was afraid she'd send him to jack off in the bathroom and go home. Up until now the rules of their game had been designed to coax him into continuing, but now she'd be operating with a toy that gave her far less feedback than her own fingers. And part of her, a small part of her, held out hope that she'd get a chance to do this again if things went well. But that meant making sure Mister Cauldwell was enjoying himself, which required at least some semblance of honest communication.

"I want you to promise me you'll tell me if something is wrong. Can you do that for me, Sam?" The slow movement of her hips persisted but she still didn't give him that fullness, the satisfaction of sliding her strap-on into him. Not yet, not until he agreed.
 
Sam couldn't believe this was happening, he had wanted to screw Catherine for so long, clearly, someone somewhere had a reasonably sick sense of humor. As he felt the head of her thick purple cock press against his ass, almost gently, like perverse, inverse Sword of Damocles waiting to... Thrust. It all felt so far from his expected possible outcomes of the evening that it couldn't possibly be happening. But it absolutely was, nothing in the world was quite as real as the phallus pressing on his asshole. He felt his cock twitch every time it moved against him.

What surprised him though was how much he wanted it, he felt like someone about to skydive excited but apprehensive. As she spoke he actually winced when she said less intense, it reminded him quite how intense this was and how much power she had over him in this moment. It was almost like the speech he'd been given by his personal trainer and he appreciated it if only for that, a means of categorizing this as a strange but difficult exercise. It seemed he'd passed some kind of gate she wasn't threatening him with being sent home anymore, what made him feel a little dirty was how proud he felt at this like he'd achieved something not to be thrown out. It was a total flip to his perceptions.

"I, I understand Miss Jones." Sam began and then, unable to keep the slightest laugh out of his voice at the absurdity of the statement added. "But please, please fuck me before I lose my nerve."

Sam didn't even realize he was doing it but he was arching his back harder, pushing back slightly and almost wiggling his ass his whole body a visual expression of eager submission. He was still nervous but he wanted this so badly, something he had never even thought about, even considered as something he would think about. More than just the new ground of his prostate, something he'd be exploring further even if he never saw Catherine again, he wanted her to take him, to make him hers. He didn't just want to fuck, he wanted to get fucked.
 
That someone somewhere was standing right behind him. Catherine had never claimed to have a proper sense of humor, and she recognized the irony in how their night had ended versus how he'd visualized it. But they were both enjoying themselves, and wasn't that what counted? Something something, the real friends they made along the way and all.

She could feel him pressing back against her, and the dildo tried to pivot downward. Her own stabilizing grip kept it exactly where it would be, but the need for stabilization telegraphed just how eager he was. Part of her wanted to hold back, see just how much more desperation she could milk out of his body language before giving him what he wanted. But the boy had a point. Drag things out too long and she risked him losing his nerve, or at least his arousal.

"As the gentleman desires," she muttered in agreement, and began to push her hips properly forwards.

The head wasn't much bigger 'round than her fingers, though anticipation had made him clench back up and gave her some resistance. But she pushed slowly and waited in the space between breaths for him to adjust and relax. Her off hand went from spreading his cheeks to petting his back, and she murmured her quiet mantra of relax, relax as she pushed into him. One, two inches went in, and then she had to pause and back off to add more lube before continuing. Three, four inches, deeper than her fingers had been able to reach with any dexterity, and certainly past his prostate, though it was easy enough to pull back the two or so inches required to strike that spot within him.

And Catherine did so with prejudice. Her thrusts were slow, and she was shallow enough that she kept her right hand on the shaft of her toy lest it try to bend, but purposeful. The roll of her hips was smooth and obviously practiced, though Sam wasn't granted an angle that could let him see the powerful muscles of her glutes and hamstrings aid in his destruction. He could only look back and up at her, see her lusty grin and the color in her cheeks and the coldness in her green eyes as she bent the chief thorn-in-her-side over the past half-year over a couch and fucked his ass.

"You're doing so well for me, Sam." She praised, adding a bit more speed. Her off hand reached around as she bent forwards and grabbed his throbbing cock, stroking him in half-time to the tempo of her thrusts. "I didn't think you'd have such a fuckable ass but here we are... mmm, do you want me to go deeper?" She'd been holding back from going too far, not sure if he'd find the deeper penetration as pleasurable. "Moan loudly if the answer is yes, Sam."
 
Sam didn't say a word as she entered him, trying his best to focus on her gentling murmuring voice to relax. He would be lying if he said the feeling was entirely pleasant, the stretching ached a little and the unstable feeling of being entered still made his guts roil a little. But running over the top of that the sheer intensity of the sensation, was all-consuming, his whole perception focused on the rubber cock slowly working into his asshole.

As Catherine worked it in and out, adding lube and working her cock back into his virgin asshole Sam was both intimately aware of every millimeter of movement and lost in his own task of focusing on relaxing. It felt so unnatural like he was surrendering to an aggressor and not only not trying to resist but actively giving in. It was an anathema to his usual mindset of dominance, of victory or nothing, but he was to wound up in the scenario, in the physical feelings, to think about it.

As the tip hit his prostate Sam's moans rose sharply in pitch, almost whining, under the intensity of it. That for a moment was too much, the intensity of the hard tap with the tip on his newly discovered most sensitive point, if it had gone on a moment longer he would have begged Catherine to stop. But the moment passed, her cock pushed deeper into him and then the underside was rubbing across it like a bow over the strings of a violin. Sam's whine was replaced with a groan, this was still incredibly uncomfortable, ring stretching and aching while his guts rolled with that same nagging instability. But none of that competed with the intense pleasure as she fucked him.

There was no denying that was what was happening, Catherine wasn't playing with his ass, or engaged in some strange foreplay she had him bent over like a slut as she fucked him. He winced horrified when she described his fuckable ass, not so much from the words themselves but from his own reaction: swelling pride that made made him arch his back harder and try to make himself more available to her powerful thrusts. As she gripped his cock and began to jerk him he lost some of his control.

Sam had been surprised by a lot of what he had said and done over the last few hours, as he willingly submitted to a rival he should by all rights be trying to crush. But he could never have predicted what he said next.

"Please, it's so big! Please fuck me Miss Jones! Please fuck my ass!" It was like someone else was speaking through his mouth, an octave higher and a level of desperation so alien he could not imagine it in himself.
 
She adored how he responded to her praise, arching his back and trying to push his hips more firmly into her thrusts. A small part of her wondered if he was simply that much a creature of his own ego, or if he got so little direct praise otherwise that what she gave him was rain to a parched desert. His line of work led to many victories and accomplishments, but the praise was implicit rather than explicit. Promotion to partner, pay raises, more lucrative and impact work; these things were granted but it was very rare for someone to tell you that you were doing a good job past a certain point. And the women he fucked likely had very little to say once he got them undressed.

Catherine had been about to say more, to encourage him to further noise, when he finally got his diaphragm enough under control to speak. Though she'd only asked him to moan she wouldn't deny that his words had a possibly greater impact, if for how unlikely they were. His voice had gone up and he sounded truly desperate, and her grip on his cock tightened reflexively as she processed that he was begging for more.

"It is big, Sam, bigger than you," she purred as she gave him what he wanted, letting her thrusts take her another half inch, full inch, two inches deeper at the bottom. Now she was pumping six inches of silicone through him, though she was careful to not draw too far back at the top. Her strokes were long and slow, matching now the tempo with which she worked his cock, drawing pleasure out of him in slow waves. "And you're taking it so well. Are you going to cum for me, Sam?"

Likely not, with the pace she'd set. But Catherine fixed that in short order, adding speed to her thrusts again as she grew more confident that he could take it. Six inches was enough of the total length that she didn't have room to grip the base any more, and put her idle hand on one of his hips to better anchor herself. Her grip was tight enough to press her nails into his skin, and he'd have little half-moon indentations when they were done, but as long as she didn't cut him she didn't much care. He was panting, groaning, whining beneath her and she was reveling in the sounds, letting her own self-control slip. Her hips moved automatically, her hand gripping the base of his shaft now to keep his cock from bobbing about wildly, and she needed to hear him cry out as she pushed him over the edge.

"Do it, Sam. Cum for me, now," she ordered when she was sure he was on the verge of finishing, and made sure he was aimed at the towel.
 
Sam had thought she was all the way in, he had felt so full then she said it, told him she wasn't just big but bigger than him. That sent a wave of embarrassment through him, the feeling of it almost pushed him over the edge. He was suddenly distracted as she somehow thrust even deeper inside of him, two inches felt like a foot and Sam groaned allowed so hard it faded into a gasp. Those words and that feeling would haunt him for weeks afterwards.

Not least because the combination of embarrassment and violation felt almost... Good. Not that Sam would find that easy to acknowledge.

Her grip on his dick was hard and the pumping regular, he felt it bringing him on closer all the time. Sam almost didn't want it to end, tried to hang on to this feeling. Till she told him not to anyway, she ordered him so cum for her and he obeyed almost instantly.

Thick white ropes splattered down on to the towel, his legs shook with the unleashed adrenaline and he shuddered from the final release. Sam leant forward resting his elbows on the back of the couch below his hands. He took long deep breaths, his cock still pulsing as it kept trying to pump out in the post organic aftershock.

"Thank you... Miss Jones" he managed between breaths. "That was..." amazing? The most humiliating thing that's ever happened to me? A unique experience? "...new" he settled on.

As his dick finally slowed the horror and the embarrassment came back like a wave. Or rather they remained exactly where they were and the tide of arousal went out revealing them. Not only had he just had sex with a very talented, aggressive and competitive member of a rival firm comprising himself, but he had allowed her to totally dominate him, to literally bend him over and fuck him in the ass. If anyone ever found out... it didn't bare thinking about.

As Catherine withdrew he felt suddenly empty, cold as the energy of fucking withdrew and he was left naked and sweaty in the cool apartment. His ass hurt now, it felt sore, bruised by the relentless pounding of Catherine's lean but powerful body. That hardly bothered him though compared to the embarrassment, he couldn't believe he had let himself be so compromised by a pretty face. That wasn't true, Catherine was a lot more than a pretty face, a worthy opponent might be a better term. Though he got the feeling whatever competition had been between them he had a fairly good idea she had just won.

In his head he recited every swearword he knew all directed at himself. After a moment it dawned on him that he still hadn't moved his hands and... he didn't want to. He had just cum harder than he ever had in his life, as acutely embarrassed and irritated with himself and his cock ad he was right now he didn't want to... throw this away, or ruin it for her or whatever. He had no idea if she had cum, if so how? Just from the power she must feel or perhaps she had a dildo on the other end of that harness. If not there were reasonable odds this wasn't over.

So Sam, his cock slowly deflating, ass open to the world, stayed put and reflected on how fucked he was. In every sense of the word.
 
When he was spent she let him go, not wanting at the moment to push him from pleasure into painful overstimulation. Her hips stilled as well as he crested the wave of his pleasure and began to come down the other side, not that she could've moved much anyway with how hard he bore down upon the phallus she'd buried inside of him. He was breathing heavily, but evenly, and she stayed quiet while he figured out just what the fuck had happened. At least he had the good sense to thank her, even if he looked and sounded as shaky as a newborn foal.

"I suspect new is an understatement." Catherine remarked as she awkwardly twisted to wipe her hand on a clean spot on the towel below. "But..." She touched at one of the globs of seed now cooling on the towel, briefly flirted with the idea of making him lick her fingers clean, then wiped them clean instead. "You certainly seemed to enjoy that. How wonderfully surprising." If he hadn't known her professionally her words and tone could've been taken as dry sarcasm, but he knew her better than that. She was gloating, the same way she had when she'd backed his team into a corner on a matter of employee seniority and retirement benefits for the Japanese employees who'd be merging into the American company's system. Only now her victory was far, far more personal.

"I'm going to pull out now." The announcement came with her hand reaffirming it's grip on his hip, the other against one buttock as she slowly pulled. She went slow, aware of how much he'd really ache once he was empty, though at the very end she could feel herself being pushed as the widest point of her toy passed his outer sphincter. Then she was free, and he could hear a faint jingle and muted click as she stepped to the side to once more explore the mysterious depths of her black duffel.

What came out was far less threatening than anything else: a travel container of baby wipes. One was used to clean off the worst of the mess on her toy, though she'd be boiling it back to sterility the next day. Then she took the harness off entirely, setting it back on the table with the business end resting on another wipe. Dressed once more in only garter and stockings, she took out another wipe, and approached Sam once more.

"Ah, I see you've remembered the first rule," she praised as she brought the wipe to press against his rear, just above his empty hole. She held it there long enough for the damp material to warm up, then proceeded downward to clean him up. Her touch was soft, even a little hesitant, as she had no idea how sore he was or wasn't yet feeling. When she was done she stepped back and clapped her hands. "You can get up now, Sam. You've been very good tonight, so I'll give you a choice as to how to proceed."

Dropping the used wipe on the table besides the harness she waited until he had dismounted from the couch, then folded up the towel he'd painted and put it aside.

"I think your cock will fit comfortably back into your pants now, so if you'd like, you can go clean up and head home. Or clean up and spend the night on the couch, I don't much care as long as you're gone by the time I wake up." He hadn't yet earned the right to sleep in the guest bedroom, and she didn't want him to get any incorrect ideas about their hook-up. She wasn't so cruel as to force him to try to find a cab at three (maybe four?) in the morning, but only barely.

She stalked around his front, sliding into the space between his body and the couch, her legs pressing against the cushion behind her. Even in heels she had to look up at him, naked, sweaty, looking utterly unsure of what he had just done. Embarrassed, even? He smelled of sex and shame and the mixture made her want to lean in and inhale, but she instead sat down on the couch and looked up expectantly. "Or..." She spread her legs once more, exposing herself, lower lips flushed and glistening with moisture. Between his work earlier and the sheer sexual power of fucking him to climax she was dripping wet, and her clit throbbed with the need for attention.

"Or you can get down on your fucking knees and finish what you started."
 
Sam cringed slightly as he recognised her gloating, when she'd used it in meetings he had felt nothing but irritation and a hardening of his own resolve. But in the new context it instilled an entirely different reaction. He felt cowed, pushed down and didn't feel any inclination to push back, it was so strange.

He dwelled on it as she cleaned him up, he felt uncomfortable but oddly grateful. The tone only reminded him he was going to be sat across from Catherine in another meeting entirely too soon and they would both know. There was no getting around it, no escaping it, this was indelibly etched on every future interaction he would have with Catherine.

Finally she told him to stand and he saw she had removed the thick purple cock and harness. Which lay discarded on the table, oddly ominous. It was much closer to his idealised visage of her now in just her stocking and garter belt. God for all this she was still so damn hot he could feel his cock twitch and pulse just from the sight of her. One thing had changed though, he tried to meet her gaze and failed, he thought he might actually be blushing a little, instead he looked down.

Whatever this feeling was it was only amplified as she gave her ultimatum. Sam's face dropped as he imagined trying to get a cab at this hour, standing on the side walk with his aching ass in the cold. Or he could sleep on the couch... as long as he was gone before she got up. He was stunned almost speechless as she walked closer, to his own internal disgust be began formulating how he was going to ask to sleep on the couch. When she offered that 'or' his mind leapt on it. Not that he was worried about sleeping on a couch... but to avoid having to ask for it.

She smelled amazing as she got closer he looked up slightly in eager anticipation of any way out of his predicament. The way she snapped out the word fucking made him tremble slightly and his cock pulse. Sam didn't hesitate, he moved immediately to stand between her legs, his cock already semi-hard and dropped to his knees.

"I, I want to finish Miss Jones." He said, not looking up her face but rather staring at her pink, perfect pussy.
 
Though he'd gone mostly soft, she caught the hint of movement from his member as she ordered him to the floor. Useful information, though while Catherine wondered just how he'd react if she pulled her domme voice on him in a meeting, she knew she wouldn't ever cross that line. Their evening had to be forgotten, and on Monday they'd go back to work and look one-another in the eye and business would be as usual. The thought was a disappointing one, but that was how it had to be. It was why he had to be gone by morning, and why they could never talk about this ever again.

Sam didn't look very interested in talking at the moment, anyway.

With him kneeling between her legs, attention rapt on her slit, she spread her thighs a little wider and leaned back. She was enjoying his look of hungry desire, and how mesmerized he appeared by a pussy he wasn't even going to get to fuck. Even after draining his balls with her hand and her strap he was at half-mast again, she noted, and wondered if they'd have the energy when she was done to debase him further. Likely not, unfortunately. She was having trouble keeping her eyes open even as things were, and that was with her cunt so wet and aching for stimulation that she was ready to hump a pillow.

"Then by all means, don't let me stop you. Do use your fingers this time as well, and make sure to clean up the mess when you're done." She ordered, shifting her hips further forward and inviting him to begin.

Her strap wasn't double-sided, and she hadn't used a vibrator, but that didn't stop her from getting hopelessly turned-on in fucking him. Sam found her eager and needy when he curled his fingers inside of her and lavished her clit with his tongue, and soon enough she had both hands on his scalp to push him more firmly to his task. And he finally got to hear the sounds he'd been hoping for, the ones he'd imagined Catherine making at his touch, soft moans that grew louder as her channel tightened around his digits. The same strength that gave shape to her body was present in her inner muscles as well, and when she finally and aggressively came, he could feel his fingers held tight as her abdomen fluttered and danced above him.

True to her word she didn't let him up until he'd licked her clean after, both hands pressing the back of his head with steady pressure until she was satisfied with the job he'd done. Then she let him go, sighing in contentment as she came down from the high of a well-earned orgasm. As the pleasure faded into a pleasant glow so did her remaining energy, leaving her utterly exhausted. She suspected Sam felt much the same.

"Up." Catherine ordered, and waved a hand to encourage him to go stand somewhere else. Then she stood, obviously shaky on her feet, and bundled the used towels under one arm alongside the strap-on, the used wipes, gloves, and bottle of lube. In the other she took the duffel, then headed off in the direction of her bedroom. A few steps in she glanced back at Sam, still naked, still standing there like an idiot with his cock hard and his eyes wide.

"You're free to go, Mister Cauldwell. Or stay, as long as I don't wake up and find you still here." She paused, lips twitching as she debated offering him the guest bedroom. But she was afraid that would send the wrong message. She split the difference, gesturing with her chin at a closet. "There's a blanket in there, and spare towels. Clean yourself up, you're a fucking mess."

And then she continued into her bedroom and bumped the door closed with her hip, the quiet click of the latch engaging the last he would hear from her until Monday.
 
You must log in or register to reply here.
Back
Top Bottom